Pd(II)-catalyzed coupling-cyclization of 1,2-allenyl phosphonic acid monoesters with allylic halides and their application to the synthesis of 1,3-dihydro[2,1]benzoxaphosphole 1-oxides

Synlett

Volumn , Issue 4, 2007, Pages 583-586

  Ma, Shengming ^a   Yu, Fei ^a   Zhao, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Coupling cyclization; Monoester; Palladium catalyzed

Indexed keywords

1 ETHOXY 1,3 DIHYDRO[2,1]BENZOXAPHOSPHOLE 1 OXIDE; 1,2 ALLENYL PHOSPHONIC ACID; 1,3 DIHYDRO[2,1]BENZOXAPHOSPHOLE 1 OXIDE; 3,4 DIALLYL 2,5 DIHYDRO[1,2]OXAPHOSPHOLE 2 OXIDE; ESTER DERIVATIVE; HALIDE; PALLADIUM; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 33947220560     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967973     Document Type: Article

References (62)

1. (a) Mader, M. M.; Bartlett, P. A. Chem. Rev. 1997, 97, 1281.
2. (b) Brassfield, H. A.; Jacobsen, R. A.; Verkade, J. G. J. Am. Chem. Soc. 1975, 97, 4143.
3. For reviews, see: (a) Brunel, J. M.; Buono, G. Top. Curr. Chem. 2002, 220, 79.
4. (b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
5. (a) Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976.
6. (b) Morita, I.; Kunimoto, K.; Tsuda, M.; Tada, S. I.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 4144.
7. (c) Stewart, J. D.; Liotta, L. J.; Benkovic, S. J. Acc. Chem. Res. 1993, 26, 396.
8. (d) Collard, J.; Benezra, C. Tetrahedron Lett. 1982, 23, 3725.
9. (e) Racha, S.; Vargeese, C.; Vemishetti, P.; El-Subbagh, H. I.; Abushanab, E.; Panzica, R. P. J. Med. Chem. 1996, 39, 1130.
10. (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
11. (b) Christov, V. C.; Prodanov, B. Heterocycles 2002, 57, 1777.
12. (c) Macomber, R. S.; Krudy, G. A. J. Org. Chem. 1983, 48, 1425.
13. (d) Cristau, H. J.; Pirat, J. L.; Virieux, D.; Monbrum, J.; Ciptadi, C.; Bekro, Y. J. Organomet. Chem. 2005, 690, 2472.
14. (e) Stachel, H. D.; Hampl, B. Chem. Ber. 1981, 114, 405.
15. (f) Hah, J.; Lee, B.; Lee, S.; Lee, H. Tetrahedron Lett. 2003, 44, 5811.
16. (g) Abramovitch, R. A.; Konieczny, M.; Pennington, W.; Kanamathareddy, S.; Vedachalam, M. J. Chem. Soc., Chem. Commun. 1990, 269.
17. For some reviews, see: (a) The Chemistry of Allenes, Vol. 1; Landor, S. R., Ed.; Academic Press: London, 1982.
18. (b) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
19. (c) Hashmi, A. S. K. Angew. Chem. Int. Ed. 2000, 112, 3590.
20. (d) Ma, S. Acc. Chem. Res. 2003, 36, 701.
21. (e) Modern Allene Chemistry, Vol. 1 and 2; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004.
22. (f) Ma, S. Chem. Rev. 2005, 105, 2829.
23. (a) Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Synlett 1999, 324.
24. (b) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904.
25. (c) Ma, S.; Jiao, N. Angew. Chem. Int. Ed. 2002, 41, 4737.
26. (d) Ma, S.; Jiao, N.; Yang, Q.; Zheng, Z. J. Org. Chem. 2004, 69, 6463.
27. (e) Hamaguchi, H.; Kosaka, S.; Ohno, H.; Tanake, T. Angew. Chem. Int. Ed. 2005, 44, 1513.
28. (f) Närhi, K.; Franzén, J.; Bäckvall, J. E. Chem. Eur. J. 2005, 11, 6937.
29. (g) Hyland, C. Tetrahedron 2005, 61, 3457.
30. (h) Parthasarathy, K.; Jeganmohan, M.; Cheng, C. Org. Lett. 2006, 8, 621.
31. (a) Kimura, M.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 3764.
32. (b) Jonasson, C.; Horvath, A.; Bäckvall, J.-E. J. Am. Chem. Soc. 2000, 122, 9600.
33. (c) Karstens, W. F. J.; Klomp, D.; Rutjes, F. P. J. T.; Hiemstra, H. Tetrahedron 2001, 57, 5123.
34. (d) Watanabe, K.; Hiroi, K. Hetrocycles 2003, 59, 453.
35. (e) Ma, S.; Li, L. Org. Lett. 2000, 2, 941.
36. (f) Ma, S.; Yu, Z. J. Org. Chem. 2003, 68, 6149.
37. (g) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104.
38. (h) Ma, S.; Yu, F.; Gao, W. J. Org. Chem. 2003, 68, 5943.
39. (i) Ohno, H.; Takeoka, Y.; Kodah, Y.; Miyamura, K.; Tanaka, T. J. Org. Chem. 2004, 69, 4541.
40. (j) Alcaide, B.; Almendros, P.; Acebes, R. R. Chem. Eur. J. 2005, 11, 5708.
41. (k) Ohno, H.; Miyamura, K.; Mizutani, T.; Kadoh, Y.; Takeoka, Y.; Hamaguchi, H.; Tanaka, T. Chem. Eur. J. 2005, 11, 3728.
42. (a) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
43. (b) Amombo, M. O.; Hausherr, A.; Reissig, H.-U. Synlett 1999, 1871.
44. (c) Dieter, R. K.; Yu, H. Org. Lett. 2001, 3, 3855.
45. (d) Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
46. (a) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. Angew. Chem. Int. Ed. 2000, 39, 2285.
47. (b) Morita, N.; Krause, N. Org. Lett. 2004, 6, 4121.
48. (c) Zhou, C.; Chan, P. W. H.; Che, C. Org. Lett. 2006, 8, 325.
49. (d) Morita, N.; Krause, N. Angew. Chem. Int. Ed. 2006, 45, 1897.
50. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molly, K. C.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1989, 1073.
51. (a) Kang, S. K.; Yoon, S. K. Chem. Commun. 2002, 2634.
52. (b) Montgomery, J.; Song, M. Org. Lett. 2002, 4, 4009.
53. (a) Yoneda, E.; Kaneko, T.; Zhang, S.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441.
54. (b) Trost, B. M.; Toste, F. D.; Prinkerton, A. B. Chem. Rev. 2001, 101, 2067.
55. (c) Kang, S. K.; Kim, K. J.; Hong, Y. T. Angew. Chem. Int. Ed. 2002, 41, 1584.
56. (d) Kang, S. K.; Kim, K. J.; Hong, Y. T. Angew. Chem. Int. Ed. 2002, 41, 1584.
57. (e) Trost, B. M.; McClory, A. Org. Lett. 2006, 8, 13627.
58. (a) Granoth, I.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 4618.
59. (b) Miles, J. A.; Grabiak, R. C.; Cummins, C. J. Org. Chem. 1982, 47, 1677.
60. Devon, T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds, Vol. 1; Academic Press: New York, 1975, 249-264.
61. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
62. Lane, C. F. Synthetic Reagents, Vol. 3; Pizey, J. S., Ed.; Ellis Horwood: Chichester, 1977, 1.